Charge transporting polymer, process for producing the same, and organic electronic device containing the same

- Fuji Xerox Co., Ltd.

A charge transporting polymer represented by formula ##STR1## wherein R represents a hydrogen atom, an alkyl group, an acyl group or --CONH--R, wherein R' represents an alkyl group or a substituted or unsubstituted aryl group; R.sub.1 and R.sub.2, which may be the same or different, each represent a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, a halogen atom, or a substituted or unsubstituted aryl group; X represents a substituted or unsubstituted divalent aromatic group; y represents 0 or 1; m represents 0 or 1; n represents an integer of 1 to 5; and p represents an integer of 5 to 5000,a process for producing the same, and an organic electron device containing the same, such as an electrophotographic photoreceptor are disclosed. The charge transporting polymer is excellent in solubility, film-forming properties, mechanical strength, positive hole mobility, and stability to repeated use.

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Claims

1. A charge transporting polymer represented by formula (I): ##STR100## wherein R represents a hydrogen atom, an alkyl group, an acyl group or --CONH--R', wherein R' represents an alkyl group or a substituted or unsubstituted aryl group; R.sub.1 and R.sub.2 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, a halogen atom, or a substituted or unsubstituted aryl group; X represents a substituted or unsubstituted divalent aromatic group; y represents 0 or 1; m represents 0 or 1; n represents an integer of 1 to 5; and p represents an integer of 5 to 5000.

2. A charge transporting polymer according to claim 1, wherein said polymer is a tetraarylbenzidine polyether represented by formula (I-1): ##STR101## wherein R represents a hydrogen atom, an alkyl group, an acyl group or --CONH--R', wherein R' represents an alkyl group or a substituted or unsubstituted aryl group; R.sub.1, R.sub.2, and R.sub.3, each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, a halogen atom, or a substituted or unsubstituted aryl group; n represents an integer of 1 to 5; and p represents an integer of 5 to 5000.

3. A process for producing a charge transporting polymer represented by formula (I): ##STR102## wherein R represents a hydrogen atom, an alkyl group, an acyl group or --CONH--R', wherein R' represents an alkyl group or a substituted or unsubstituted aryl group; R.sub.1 and R.sub.2, each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, a halogen atom, or a substituted or unsubstituted aryl group; X represents a substituted or unsubstituted divalent aromatic group; y represents 0 or 1; m represents 0 or 1; n represents an integer of 1 to 5; and p represents an integer of 5 to 5000,

which comprises intermolecular condensation of a charge transporting compound having a hydroxyl group, the charge transporting compound being represented by formula (II): ##STR103## wherein R.sub.1, R.sub.2, X, y, m, and n are as defined above.

4. A process for producing a charge transporting polymer according to claim 3, wherein the charge transporting compound represented by formula (II) is a compound represented by formula (II-1): ##STR104## wherein R.sub.1, R.sub.2, and R.sub.3, each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, a halogen atom, or a substituted or unsubstituted aryl group; n represents an integer of 1 to 5.

5. A charge transporting polymer according to claim 1, wherein the aryl group contains from 6 to 12 carbon atoms and is substituted with a substituent selected from the group consisting of an alkyl group containing from 1 to 4 carbon atoms, an alkoxy group containing from 1 to 4 carbon atoms, a biphenyl group and a naphthyl group.

6. A charge transporting polymer according to claim 1, wherein the amino group is substituted with a substituent selected from the group consisting of an alkyl group containing from 1 to 4 carbon atoms and a phenyl group.

7. A charge transporting polymer according to claim 1, wherein the divalent aromatic group is substituted with a substituent selected from the group consisting of an alkyl group having from 1 to 4 carbon atoms, a phenyl group, an aralkyl group, an alkoxy group having from 1 to 4 carbon atoms and a halogen atom.

8. A charge transporting polymer according to claim 2, wherein the aryl group contains from 6 to 12 carbon atoms and is substituted with a substituent selected from the group consisting of an alkyl group containing from 1 to 4 carbon atoms, an alkoxy group containing from 1 to 4 carbon atoms, a biphenyl group and a naphthyl group.

9. A charge transporting polymer according to claim 2, wherein the amino group is substituted with a substituent selected from the group consisting of an alkyl group containing from 1 to 4 carbon atoms and a phenyl group.

10. A process for producing a charge transporting polymer according to claim 3, wherein the aryl group contains from 6 to 12 carbon atoms and is substituted with a substituent selected from the group consisting of an alkyl group containing from 1 to 4 carbon atoms, an alkoxy group containing from 1 to 4 carbon atoms, a biphenyl group and a naphthyl group.

11. A process for producing a charge transporting polymer according to claim 3, wherein the amino group is substituted with a substituent selected from the group consisting of an alkyl group containing from 1 to 4 carbon atoms and a phenyl group.

12. A process for producing a charge transporting polymer according to claim 3, wherein the divalent aromatic group is substituted with a substituent selected from the group consisting of an alkyl group having from 1 to 4 carbon atoms, a phenyl group, an aralkyl group, an alkoxy group having from 1 to 4 carbon atoms and a halogen atom.

13. A process for producing a charge transporting polymer according to claim 4, wherein the aryl group contains from 6 to 12 carbon atoms and is substituted with a substituent selected from the group consisting of an alkyl group containing from 1 to 4 carbon atoms, an alkoxy group containing from 1 to 4 carbon atoms, a biphenyl group and a naphthyl group.

14. A process for producing a charge transporting polymer according to claim 4, wherein the amino group is substituted with a substituent selected from the group consisting of an alkyl group containing from 1 to 4 carbon atoms and a phenyl group.

Referenced Cited
U.S. Patent Documents
4801517 January 31, 1989 Frechet et al.
4806443 February 21, 1989 Yanus et al.
4806444 February 21, 1989 Yanus et al.
4937165 June 26, 1990 Ong et al.
4959288 September 25, 1990 Ong et al.
4983482 January 8, 1991 Ong et al.
5034296 July 23, 1991 Ong et al.
5409792 April 25, 1995 Yanus et al.
5436099 July 25, 1995 Schank et al.
Foreign Patent Documents
295 113 December 1988 EPX
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Other references
  • Murti et al., "Charge Transport Polymers Based on Triphenylamine and Tetraphenylbenzidine Moieties", from the proceedings of The Sixth International Congress on Advances in Non-Impact Printing Technologies, Oct. 21-26, 1990, pp. 306-311.
Patent History
Patent number: 5734003
Type: Grant
Filed: Dec 11, 1996
Date of Patent: Mar 31, 1998
Assignee: Fuji Xerox Co., Ltd. (Tokyo)
Inventors: Masahiro Iwasaki (Minami-ashigara), Akira Imai (Minami-ashigara), Katsumi Nukada (Minami-ashigara), Katsuhiro Sato (Minami-ashigara)
Primary Examiner: John M. Cooney, Jr.
Law Firm: Oliff & Berridge, PLC
Application Number: 8/763,887